We present here synthesis and crystal structure of a neutral Ir
III complex, [Ir(C
19H
13N
2)
2(C
15H
11O
2)]·2CH
2Cl
2 or [Ir(C^N)
2O^O]·2CH
2Cl
2, where C^N is 1,2-diphenyl-1
H-benzimidazole and O^O is 2-benzoyl-1-phenylethenolate. The coordination sphere of the Ir
III atom, located on a twofold rotation axis, is that of a slighlty distorted C
2N
2O
2 octahedron, with the N atoms in a
trans configuration. In the crystal, complex molecules assemble through weak C—H

π interactions in the range 2.699 (3)–2.892 (3) Å. The solvent CH
2Cl
2 molecules reside in channels aligned along the
a axis and are connected to the complex molecules by C—H

O interactions.
Supporting information
CCDC reference: 1517541
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.018
- wR factor = 0.043
- Data-to-parameter ratio = 20.6
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.31 Report
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C31 Check
Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 6.30 Why ?
PLAT432_ALERT_2_G Short Inter X...Y Contact Cl2 .. C11 .. 3.24 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(2-Benzoyl-1-phenylethenolato-
κ2O,
O')bis[2-(1-phenyl-1
H-benzimidazol-2-yl)phenyl-
κC1]iridium(III)
dichloromethane disolvate
top
Crystal data top
[Ir(C19H13N2)2(C15H11O2)]·2CH2Cl2 | Dx = 1.605 Mg m−3 |
Mr = 1123.92 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Aba2 | Cell parameters from 9873 reflections |
a = 13.9159 (7) Å | θ = 2.2–30.5° |
b = 25.5352 (12) Å | µ = 3.15 mm−1 |
c = 13.0898 (6) Å | T = 150 K |
V = 4651.4 (4) Å3 | Plate, orange |
Z = 4 | 0.40 × 0.25 × 0.15 mm |
F(000) = 2240 | |
Data collection top
Bruker SMART APEXII diffractometer | 5029 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
ω scans | θmax = 29.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −18→18 |
| k = −34→34 |
21901 measured reflections | l = −17→17 |
6169 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.018 | w = 1/[σ2(Fo2) + (0.0163P)2 + 6.3016P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.043 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 1.07 e Å−3 |
6169 reflections | Δρmin = −0.46 e Å−3 |
299 parameters | Absolute structure: Flack x determined using 2201 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.007 (3) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ir1 | 0.0000 | 0.0000 | 0.87622 (4) | 0.01596 (4) | |
O1 | −0.0422 (2) | 0.05472 (12) | 0.7569 (2) | 0.0202 (6) | |
N1 | −0.12555 (19) | −0.04069 (10) | 0.8901 (2) | 0.0173 (6) | |
N2 | −0.2133 (2) | −0.10159 (12) | 0.9688 (2) | 0.0202 (6) | |
C1 | 0.0377 (3) | −0.05237 (16) | 0.9825 (3) | 0.0169 (8) | |
C2 | 0.1284 (3) | −0.06017 (15) | 1.0264 (3) | 0.0206 (7) | |
H6A | 0.1799 | −0.0378 | 1.0070 | 0.025* | |
C3 | 0.1456 (3) | −0.09984 (15) | 1.0979 (3) | 0.0250 (8) | |
H5A | 0.2084 | −0.1044 | 1.1250 | 0.030* | |
C4 | 0.0721 (3) | −0.13256 (18) | 1.1296 (3) | 0.0261 (10) | |
H4A | 0.0839 | −0.1586 | 1.1798 | 0.031* | |
C5 | −0.0197 (3) | −0.12704 (16) | 1.0873 (3) | 0.0238 (8) | |
H3A | −0.0704 | −0.1496 | 1.1076 | 0.029* | |
C6 | −0.0357 (3) | −0.08776 (15) | 1.0147 (3) | 0.0199 (7) | |
C7 | −0.1252 (3) | −0.07847 (14) | 0.9607 (3) | 0.0187 (7) | |
C8 | −0.2463 (3) | −0.14125 (14) | 1.0383 (3) | 0.0209 (7) | |
C9 | −0.2713 (3) | −0.12733 (17) | 1.1363 (3) | 0.0312 (10) | |
H15A | −0.2627 | −0.0923 | 1.1591 | 0.037* | |
C10 | −0.3093 (3) | −0.16477 (19) | 1.2019 (3) | 0.0385 (11) | |
H16A | −0.3261 | −0.1556 | 1.2699 | 0.046* | |
C11 | −0.3226 (3) | −0.21529 (18) | 1.1675 (4) | 0.0346 (10) | |
H17A | −0.3492 | −0.2409 | 1.2119 | 0.042* | |
C12 | −0.2977 (4) | −0.22885 (18) | 1.0693 (4) | 0.0403 (11) | |
H19A | −0.3065 | −0.2638 | 1.0464 | 0.048* | |
C13 | −0.2600 (3) | −0.19165 (17) | 1.0038 (3) | 0.0360 (10) | |
H18A | −0.2437 | −0.2008 | 0.9356 | 0.043* | |
C14 | −0.2745 (3) | −0.07636 (14) | 0.8998 (2) | 0.0208 (8) | |
C15 | −0.3710 (2) | −0.08408 (13) | 0.8788 (4) | 0.0246 (6) | |
H12A | −0.4077 | −0.1102 | 0.9127 | 0.029* | |
C16 | −0.4109 (3) | −0.05164 (17) | 0.8058 (3) | 0.0271 (8) | |
H11A | −0.4769 | −0.0555 | 0.7889 | 0.033* | |
C17 | −0.3568 (3) | −0.01333 (15) | 0.7562 (3) | 0.0244 (8) | |
H10A | −0.3870 | 0.0079 | 0.7060 | 0.029* | |
C18 | −0.2600 (3) | −0.00515 (14) | 0.7776 (3) | 0.0219 (7) | |
H9A | −0.2237 | 0.0213 | 0.7441 | 0.026* | |
C19 | −0.2191 (2) | −0.03793 (14) | 0.8509 (2) | 0.0179 (7) | |
C20 | 0.0000 | 0.0000 | 0.6161 (4) | 0.0263 (11) | |
H21A | 0.0000 | 0.0000 | 0.5435 | 0.032* | |
C21 | −0.0349 (3) | 0.04551 (14) | 0.6622 (3) | 0.0194 (7) | |
C22 | −0.0652 (3) | 0.08839 (15) | 0.5905 (3) | 0.0213 (7) | |
C23 | −0.0429 (3) | 0.13971 (18) | 0.6134 (3) | 0.0290 (10) | |
H24A | −0.0113 | 0.1478 | 0.6759 | 0.035* | |
C24 | −0.0662 (4) | 0.17976 (18) | 0.5457 (4) | 0.0381 (11) | |
H25A | −0.0493 | 0.2149 | 0.5614 | 0.046* | |
C25 | −0.1137 (3) | 0.16867 (17) | 0.4558 (3) | 0.0362 (10) | |
H26A | −0.1301 | 0.1961 | 0.4100 | 0.043* | |
C26 | −0.1373 (3) | 0.11718 (17) | 0.4325 (3) | 0.0294 (9) | |
H27A | −0.1708 | 0.1094 | 0.3711 | 0.035* | |
C27 | −0.1123 (3) | 0.07730 (16) | 0.4986 (3) | 0.0243 (8) | |
H28A | −0.1272 | 0.0421 | 0.4815 | 0.029* | |
C31 | 0.1018 (3) | 0.32965 (17) | 0.3649 (4) | 0.0386 (11) | |
H31A | 0.0838 | 0.3634 | 0.3331 | 0.046* | |
H31B | 0.1283 | 0.3370 | 0.4336 | 0.046* | |
Cl1 | −0.00094 (11) | 0.28980 (5) | 0.3765 (3) | 0.0586 (3) | |
Cl2 | 0.18966 (10) | 0.29873 (7) | 0.28987 (11) | 0.0620 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ir1 | 0.01740 (7) | 0.01518 (7) | 0.01531 (6) | 0.00053 (8) | 0.000 | 0.000 |
O1 | 0.0239 (16) | 0.0183 (16) | 0.0183 (13) | 0.0011 (12) | 0.0007 (12) | 0.0014 (12) |
N1 | 0.0189 (12) | 0.0176 (13) | 0.0153 (17) | 0.0023 (10) | −0.0004 (11) | 0.0010 (12) |
N2 | 0.0207 (15) | 0.0215 (15) | 0.0184 (14) | −0.0016 (12) | −0.0006 (12) | 0.0039 (12) |
C1 | 0.023 (2) | 0.015 (2) | 0.0127 (16) | 0.0016 (16) | 0.0002 (15) | −0.0030 (14) |
C2 | 0.0211 (17) | 0.0209 (18) | 0.0200 (17) | 0.0011 (14) | −0.0008 (14) | −0.0009 (14) |
C3 | 0.0244 (19) | 0.026 (2) | 0.0248 (19) | 0.0071 (15) | −0.0053 (15) | −0.0015 (15) |
C4 | 0.029 (2) | 0.029 (2) | 0.0205 (18) | 0.0084 (17) | −0.0044 (16) | 0.0054 (16) |
C5 | 0.025 (2) | 0.025 (2) | 0.0208 (17) | 0.0004 (14) | 0.0028 (14) | 0.0046 (15) |
C6 | 0.0203 (16) | 0.0210 (19) | 0.0183 (17) | 0.0030 (15) | −0.0001 (14) | 0.0001 (14) |
C7 | 0.0212 (17) | 0.0172 (17) | 0.0177 (17) | 0.0007 (13) | −0.0001 (13) | −0.0006 (14) |
C8 | 0.0178 (16) | 0.0234 (18) | 0.0214 (17) | −0.0011 (14) | 0.0006 (13) | 0.0050 (15) |
C9 | 0.039 (3) | 0.030 (2) | 0.025 (2) | −0.0131 (17) | 0.0054 (19) | −0.0043 (17) |
C10 | 0.045 (3) | 0.050 (3) | 0.0197 (19) | −0.016 (2) | 0.0026 (18) | 0.0027 (19) |
C11 | 0.035 (2) | 0.034 (2) | 0.035 (2) | −0.0056 (18) | 0.0003 (19) | 0.0153 (19) |
C12 | 0.056 (3) | 0.019 (2) | 0.047 (3) | −0.003 (2) | 0.011 (2) | 0.0046 (19) |
C13 | 0.048 (3) | 0.025 (2) | 0.034 (2) | −0.0034 (19) | 0.016 (2) | −0.0020 (18) |
C14 | 0.0225 (17) | 0.0207 (17) | 0.019 (2) | 0.0036 (13) | −0.0003 (12) | 0.0006 (12) |
C15 | 0.0214 (15) | 0.0263 (16) | 0.0261 (16) | −0.0036 (12) | 0.003 (2) | 0.003 (2) |
C16 | 0.0193 (18) | 0.033 (2) | 0.029 (2) | 0.0011 (16) | −0.0023 (15) | 0.0007 (17) |
C17 | 0.0247 (18) | 0.026 (2) | 0.0222 (17) | 0.0053 (14) | −0.0022 (15) | 0.0028 (14) |
C18 | 0.0244 (17) | 0.0218 (19) | 0.0195 (15) | 0.0015 (15) | 0.0016 (13) | 0.0014 (15) |
C19 | 0.0184 (16) | 0.0188 (16) | 0.0166 (17) | 0.0016 (13) | −0.0006 (11) | −0.0004 (12) |
C20 | 0.034 (3) | 0.028 (3) | 0.017 (2) | 0.008 (3) | 0.000 | 0.000 |
C21 | 0.0167 (15) | 0.0215 (18) | 0.0202 (16) | 0.0004 (14) | 0.0001 (14) | 0.0021 (14) |
C22 | 0.0217 (17) | 0.0227 (19) | 0.0196 (16) | 0.0022 (14) | 0.0011 (14) | 0.0035 (14) |
C23 | 0.035 (2) | 0.026 (2) | 0.026 (2) | −0.0007 (19) | −0.0047 (19) | −0.0026 (18) |
C24 | 0.055 (3) | 0.021 (2) | 0.038 (2) | −0.0029 (19) | −0.007 (2) | 0.0073 (18) |
C25 | 0.045 (3) | 0.028 (2) | 0.036 (2) | 0.0024 (19) | −0.006 (2) | 0.0135 (19) |
C26 | 0.032 (2) | 0.034 (2) | 0.0227 (19) | 0.0030 (18) | −0.0063 (16) | 0.0050 (16) |
C27 | 0.0248 (19) | 0.0247 (19) | 0.0235 (19) | 0.0007 (15) | −0.0011 (15) | 0.0016 (15) |
C31 | 0.049 (2) | 0.033 (2) | 0.034 (3) | 0.0042 (17) | −0.008 (2) | −0.007 (2) |
Cl1 | 0.0683 (7) | 0.0556 (6) | 0.0518 (6) | −0.0168 (7) | −0.0125 (7) | 0.0098 (18) |
Cl2 | 0.0531 (8) | 0.0838 (11) | 0.0490 (7) | 0.0266 (8) | −0.0111 (6) | −0.0246 (7) |
Geometric parameters (Å, º) top
Ir1—C1i | 1.999 (4) | C12—H19A | 0.9500 |
Ir1—C1 | 1.999 (4) | C13—H18A | 0.9500 |
Ir1—N1i | 2.041 (3) | C14—C15 | 1.386 (5) |
Ir1—N1 | 2.041 (3) | C14—C19 | 1.402 (5) |
Ir1—O1i | 2.176 (3) | C15—C16 | 1.381 (6) |
Ir1—O1 | 2.176 (3) | C15—H12A | 0.9500 |
O1—C21 | 1.267 (5) | C16—C17 | 1.395 (6) |
N1—C7 | 1.337 (4) | C16—H11A | 0.9500 |
N1—C19 | 1.400 (4) | C17—C18 | 1.392 (5) |
N2—C7 | 1.365 (5) | C17—H10A | 0.9500 |
N2—C14 | 1.398 (4) | C18—C19 | 1.395 (5) |
N2—C8 | 1.436 (5) | C18—H9A | 0.9500 |
C1—C2 | 1.402 (6) | C20—C21i | 1.397 (4) |
C1—C6 | 1.427 (6) | C20—C21 | 1.397 (4) |
C2—C3 | 1.400 (5) | C20—H21A | 0.9500 |
C2—H6A | 0.9500 | C21—C22 | 1.502 (5) |
C3—C4 | 1.385 (6) | C22—C23 | 1.380 (6) |
C3—H5A | 0.9500 | C22—C27 | 1.400 (5) |
C4—C5 | 1.399 (5) | C23—C24 | 1.392 (6) |
C4—H4A | 0.9500 | C23—H24A | 0.9500 |
C5—C6 | 1.400 (5) | C24—C25 | 1.379 (6) |
C5—H3A | 0.9500 | C24—H25A | 0.9500 |
C6—C7 | 1.451 (5) | C25—C26 | 1.389 (6) |
C8—C9 | 1.377 (5) | C25—H26A | 0.9500 |
C8—C13 | 1.377 (5) | C26—C27 | 1.380 (5) |
C9—C10 | 1.389 (6) | C26—H27A | 0.9500 |
C9—H15A | 0.9500 | C27—H28A | 0.9500 |
C10—C11 | 1.379 (7) | C31—Cl2 | 1.755 (5) |
C10—H16A | 0.9500 | C31—Cl1 | 1.762 (5) |
C11—C12 | 1.375 (7) | C31—H31A | 0.9900 |
C11—H17A | 0.9500 | C31—H31B | 0.9900 |
C12—C13 | 1.383 (6) | | |
| | | |
C1i—Ir1—C1 | 91.9 (2) | C11—C12—C13 | 120.1 (4) |
C1i—Ir1—N1i | 79.76 (15) | C11—C12—H19A | 119.9 |
C1—Ir1—N1i | 93.11 (15) | C13—C12—H19A | 119.9 |
C1i—Ir1—N1 | 93.11 (15) | C8—C13—C12 | 119.4 (4) |
C1—Ir1—N1 | 79.76 (15) | C8—C13—H18A | 120.3 |
N1i—Ir1—N1 | 169.81 (18) | C12—C13—H18A | 120.3 |
C1i—Ir1—O1i | 177.96 (17) | C15—C14—N2 | 130.7 (4) |
C1—Ir1—O1i | 89.94 (10) | C15—C14—C19 | 122.8 (3) |
N1i—Ir1—O1i | 99.17 (12) | N2—C14—C19 | 106.4 (3) |
N1—Ir1—O1i | 88.17 (12) | C16—C15—C14 | 116.2 (4) |
C1i—Ir1—O1 | 89.94 (10) | C16—C15—H12A | 121.9 |
C1—Ir1—O1 | 177.96 (17) | C14—C15—H12A | 121.9 |
N1i—Ir1—O1 | 88.17 (12) | C15—C16—C17 | 121.7 (4) |
N1—Ir1—O1 | 99.17 (12) | C15—C16—H11A | 119.1 |
O1i—Ir1—O1 | 88.29 (16) | C17—C16—H11A | 119.1 |
C21—O1—Ir1 | 124.2 (3) | C18—C17—C16 | 122.3 (4) |
C7—N1—C19 | 107.0 (3) | C18—C17—H10A | 118.9 |
C7—N1—Ir1 | 115.2 (2) | C16—C17—H10A | 118.9 |
C19—N1—Ir1 | 137.5 (2) | C17—C18—C19 | 116.3 (3) |
C7—N2—C14 | 107.3 (3) | C17—C18—H9A | 121.8 |
C7—N2—C8 | 129.8 (3) | C19—C18—H9A | 121.8 |
C14—N2—C8 | 122.6 (3) | C18—C19—N1 | 131.4 (3) |
C2—C1—C6 | 115.7 (4) | C18—C19—C14 | 120.6 (3) |
C2—C1—Ir1 | 128.1 (3) | N1—C19—C14 | 108.0 (3) |
C6—C1—Ir1 | 116.2 (3) | C21i—C20—C21 | 128.8 (5) |
C3—C2—C1 | 122.1 (4) | C21i—C20—H21A | 115.6 |
C3—C2—H6A | 119.0 | C21—C20—H21A | 115.6 |
C1—C2—H6A | 119.0 | O1—C21—C20 | 127.3 (4) |
C4—C3—C2 | 120.7 (4) | O1—C21—C22 | 117.0 (3) |
C4—C3—H5A | 119.6 | C20—C21—C22 | 115.8 (3) |
C2—C3—H5A | 119.6 | C23—C22—C27 | 119.0 (4) |
C3—C4—C5 | 119.7 (4) | C23—C22—C21 | 119.5 (4) |
C3—C4—H4A | 120.2 | C27—C22—C21 | 121.4 (3) |
C5—C4—H4A | 120.2 | C22—C23—C24 | 120.4 (4) |
C4—C5—C6 | 119.1 (4) | C22—C23—H24A | 119.8 |
C4—C5—H3A | 120.4 | C24—C23—H24A | 119.8 |
C6—C5—H3A | 120.4 | C25—C24—C23 | 120.3 (4) |
C5—C6—C1 | 122.7 (4) | C25—C24—H25A | 119.9 |
C5—C6—C7 | 125.8 (4) | C23—C24—H25A | 119.9 |
C1—C6—C7 | 111.5 (3) | C24—C25—C26 | 119.7 (4) |
N1—C7—N2 | 111.2 (3) | C24—C25—H26A | 120.2 |
N1—C7—C6 | 117.3 (3) | C26—C25—H26A | 120.2 |
N2—C7—C6 | 131.5 (3) | C27—C26—C25 | 120.1 (4) |
C9—C8—C13 | 120.8 (4) | C27—C26—H27A | 119.9 |
C9—C8—N2 | 119.3 (3) | C25—C26—H27A | 119.9 |
C13—C8—N2 | 119.7 (3) | C26—C27—C22 | 120.5 (4) |
C8—C9—C10 | 119.6 (4) | C26—C27—H28A | 119.8 |
C8—C9—H15A | 120.2 | C22—C27—H28A | 119.8 |
C10—C9—H15A | 120.2 | Cl2—C31—Cl1 | 110.7 (3) |
C11—C10—C9 | 119.6 (4) | Cl2—C31—H31A | 109.5 |
C11—C10—H16A | 120.2 | Cl1—C31—H31A | 109.5 |
C9—C10—H16A | 120.2 | Cl2—C31—H31B | 109.5 |
C12—C11—C10 | 120.5 (4) | Cl1—C31—H31B | 109.5 |
C12—C11—H17A | 119.8 | H31A—C31—H31B | 108.1 |
C10—C11—H17A | 119.8 | | |
Symmetry code: (i) −x, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31A···O1ii | 0.99 | 2.39 | 3.377 (6) | 179 |
Symmetry code: (ii) −x, −y+1/2, z−1/2. |